Oscar Valladares has made a name for himself making unique cigars. There’s the Leaf by Oscar (wrapped in a tobacco leaf rather than cello), the Big Johnny (an 8” x 66 version of the Leaf Maduro) and the Island Jim No. 2 (that looks like a No. 2 pencil). Now, Oscar has released a cigar (mainly for events) that is a massive 21” x 100 vitola, and comes in individual coffins. While the Woody is more for show than anything else, it is a smokeable cigar and is actually surprisingly good.

At ToastedFoot, we love a good challenge. (Or at least I do, Willy won’t smoke anything bigger than a 54 ring gauge.) Knowing that there will be plenty of people that see the Woody by Oscar at events and wonder if it’s actually any good, I decided to sit and find out for myself if the Woody had more to it than just size. Over the course of three and a half hours I discovered that the Woody is a fairly flavorful cigar. Since the Woody is the longest cigar that has ever been featured on ToastedFoot, it deserved the longest review we’ve ever posted.

Pre-Light: Obviously, the size of the Woody makes this an intimidating cigar. At 21 inches long and with a 100 ring gauge, the Woody by Oscar is the largest cigar to ever appear on ToastedFoot. Oddly enough, for a cigar as big as the Woody, the cigar does not way much at all. (I have 6 inch cigars in my humidor that weigh more.) What’s most impressive is how well made the Woody appears to be, it looks like a massively scaled up Leaf by Oscar. There a slight oiliness to the dark brown wrapper of the cigar. Like the Leaf by Oascar, the Woody has a pounded agave band on it. The cigar comes in its own cedar coffin, hence the name Woody by Oscar.

There’s a strong barnyard and natural tobacco aroma to the Honduran wrapper. From the unlit foot of the cigar there is mostly natural tobacco, hay and coffee scents. The cold draw is surprisingly easy for a 21 inch cigar, and allows through some earth and coffee notes. The cigar does feel a little soft, as if it is sort of but not quite under filled.

Burn: I found lighting the Woody a bit difficult (even at 6’6” with very long arms), so I had my buddy Tony help me light it after I thoroughly toasted the foot. The draw on the Woody is very easy due mostly to its large ring gauge. During the first quarter of the cigar the smoke production is not stellar, but it does begin to put out massive amount of smoke after the halfway point. The Woody has a surprisingly good burn when you take everything into consideration. In the fourth quarter or so the burn begins to canoe a little, and needs a little correcting. The burn could have gone uneven because by the end of the cigar I was smoking rather fast to try and get through it.

Flavor: The Woody by Oscar is actually a surprisingly flavorful cigar. Most gimmicky cigars tend to lack flavor, but I found this had way more flavor and complexity than even most 7” x 70 or 6” x 62 sized cigars. The first quarter of the Woody starts out with some nice sweet earth notes that are joined by natural tobacco, nut and wood. About two inched into the cigar a background spice begins to occur on the palette. On the retrohale, there is pleasingly sweet mix of earth and coffee. The transition to the second quarter of the Woody sees the strength pick up somewhat. A barnyard hay and caramel note joins the earth, nut and wood flavors.

A steak like meatiness starts to take shape at the start of the second quarter of the Woody by Oscar. The meatiness blends well with the existing earthy flavors of the cigar. Wood, nuts, earth, caramel and leather round out the flavor profile throughout most of the second quarter of the cigar. Some very mild black pepper begins to creep onto the palette during this point in the cigar, but is not overbearing or distracting from the other flavors. On the retrohale there is a mix black pepper and coffee. Approaching the halfway point in the cigar, the cigar is solidly full bodied with a fair amount of strength to it, yet the flavors are still very pleasing.

At the transition to the third quarter of the cigar the steak like meatiness begins to morph into something more resembling meat loaf. The black pepper becomes much more prominent at this point. During the third quarter of the cigar there’s a mix of meatloaf, cedar, coffee, cocoa, earth and black pepper throughout. For a cigar this wide and this long, there’s a surprising amount of flavor. The pepper of the retrohale has mellowed somewhat, making coffee, caramel and meat the main notes on the nose. Towards the end of the third quarter of the Woody by Oscar there a really nice chocolate flavor that leads into the more peppery transition to the final quarter of the cigar. At this point in the cigar, the nicotine is finally beginning to take its toll.

The transition to the last quarter of the cigar is very earthy and peppery. During the fourth quarter of the cigar the flavors become much less pronounced. (This could be because my palette is pretty shot by this point.) The main detectable flavors during the final quarter of the cigar are pepper, earth and meat with the occasional cedar note. This is now a very very full bodied cigar. With about two inches left in cigar a bitterness begins to drown out any real distinguishable flavors. The retrohale is predominantly peppery and meaty at this point in the cigar. With an inch and a half left the bitterness (and the massive amount of nicotine coursing through my veins) has makes it easily apparent that it is time to call it quits on the Woody.

Overall: I began the review of this cigar with no other thought in mid than I wanted to be one of the only people (or the only person) to review it. I knew there’d be plenty of people wondering if it was actually any good, and there’d be a lack of people crazy enough to try it. I figured the cigar was nothing more than a novelty (and honestly it is), but I wasn’t expecting it to actually be a decent cigar with the amount of flavor it ended up having. I should have know better since it was coming from Oscar Valladares. I enjoy Oscar’s other cigars (especially the Leaf Sumatra and Maduro), and found the Woody by Oscar to be a cigar with many similarities to his other blends (albeit a scaled up version). The Woody is surprisingly flavorful, with a predominantly earth and meat core accented by cedar, nut, caramel, coffee and pepper notes. Though the cigar starts off medium bodied, it finishes in the very full bodied range. The massive amount of nicotine in this cigar does make it a bit daunting to get through, even for someone who smokes 3 to 6 cigars a day.

Personally, I’m glad I smoked it and wish the had the cigar equivalent of a 26.2 bumper sticker for people that’ve actually made it through this cigar. It was a different experience, and made me feel like I had something to prove in trying to make it all the way through. While I’m not going to smoke another one, I don’t regret smoking it at all and kind of enjoyed it. If you like Oscar Valladares’ cigars and you’re at one of his events, and you’re brave enough to try it, the cigar is actually pretty decent. This cigar makes for a great gift for those cigar smokers that already have almost everything else under the sun in their humidors.

Pairing: If you’re brave enough to smoke the Woody, then pair it with whatever you feel like drinking. Whenever I review a cigar for this site, I smoke at least one while drinking a sparkling water (normally San Pellegrino). I did drink a whole 750 ml bottle sparkling water with the Woody, but also found I need to drink two cans of regular Coca-Cola to counteract some of the effects of the nicotine in my system. I strongly recommend having a sugary drink like a Coke or Gatorade nearby while smoking the Woody. Also, don’t go into this cigar while on an empty stomach. Eat a hearty breakfast, and (if you can) have something to nibble on while smoking the cigar.

On a side note: Smoking the Woody by Oscar is the cigar smoking equivalent of a marathon. It took me three and a half hours, and I was smoking very quickly. Set aside a good four to five hours if you intend to smoke it. I smoked the Woody up at Stogies World Class Cigars in Houston, and made an event out of it. It became a spectator event, and it made the smoking of it more enjoyable. With onlookers asking questions and cheering me on, it became a social event that made the time pass more easily. (My favorite question was, “Is that a real cigar?” No, I’m smoking a fake one.) If you’re going to smoke the Woody, then do it with people around. This is a cigar that was meant to be shown off, so show it off.

A note on the review: I chose not to assign the Woody an overall number rating. If I were to give it a number rating it would fall in the 7.9 to 8.4 range, which (if you look at our scoring info) puts it in the “seek out and smoke again” category. However, the Woody by Oscar is not a cigar I plan to seek out and smoke again. Rating it lower and calling it “average, worth another try” doesn’t make sense either since nothing about this cigar is average. So, I’ve choose to say simply that it was “Good”, and to let the body of the review speak for itself. I don’t want to discourage people from trying the cigar with a lower rating, because it is a singular experience for the cigar enthusiast. This is a unique cigar, and deserves a unique review to match.

Also, typically I smoke at least two (normally three to four) cigars for a review. At least one I pair with sparkling water, one I take pictures of and the others I pair with a variety of beverage choices. The Woody is just too big (and too expensive) for me to do this with, so I only smoked one for this review. I did also stop halfway through the cigar to quickly scarf down two breakfast tacos, but I cleansed my palette with some sparkling water before returning to the cigar.

The cigar for this review was provided by Oscar Valladares and “Island Jim” Robinson of Oscar Valladares Tobacco & Co. during their event at Stogies World Class Cigars in Houston. ToastedFoot was willing to pay for the cigar, but they were generous enough to give us one for the review. While the generosity of Oscar and Jim is greatly appreciated, it does not effect the review of this cigar. No request was made for review. We at ToastedFoot remain committed to providing impartial cigar reviews.

Some photos for this review were taken by Lara Bonham (@liberty_belle_lara) of Stogies World Class Cigars in Houston, Texas. Her help in documenting this daunting cigar smoking undertaking is greatly appreciated.